Process for preparing cyclododecanone

ABSTRACT

Cyclododecanone (CDON) is prepared by epoxidizing cyclododecene (CDEN) to epoxycyclododecane (CDAN epoxide), and rearranging the CDAN epoxide to CDON to obtain a mixture comprising said CDON and cyclododecane (CDAN), wherein CDAN is separated from the CDON-containing mixture and oxidized to CDON.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a process for preparingcyclododecanone, to a process for preparing laurolactam and to a processfor preparing nylon-12.

2. Discussion of the Background

Cyclododecanone (CDON) is used for the synthesis of laurolactam. Thelactam in turn is suitable for the preparation of nylon-12.

The preparation of CDON may proceed from cyclododecatriene (CDT). Firstof all, a selective hydrogenation of cyclododecatriene (CDT) tocyclododecene (CDEN) may be undertaken. This is followed by anepoxidation of CDEN to epoxycyclododecane (CDAN epoxide) and therearrangement of CDAN epoxide to cyclododecanone (CDON). Proceeding fromCDEN, the CDON synthesis comprises the following steps:

-   -   a. epoxidizing cyclododecene (CDEN) to epoxycyclododecane (CDAN        epoxide) and    -   b. rearranging the CDAN epoxide to CDON to obtain a mixture        comprising cyclododecane (CDAN).

The mixture (CDON-containing mixture) which is obtained from therearrangement thus comprises at least CDON and CDAN.

In this process for preparing CDON, the problem occurs that significantamounts of CDAN or CDEN can arise. This problem is aggravated by theageing of catalysts which may be used. The amount of by-productsobtained may be more than 20% by weight, based on the resultingCDON-containing mixture from the rearrangement.

The high proportion of CDAN may have adverse effects on the downstreamreactions such as the preparation of laurolactam.

SUMMARY OF THE INVENTION

In this respect, the problem addressed by the present invention was thatof providing a novel process for preparing CDON which reduces theproportion of CDAN in the CDON end product. In addition, the preparationprocess was to appear more economically viable overall.

The present invention encompasses in one embodiment a process forpreparing cyclododecanone (CDON) by a reaction route I, said reactionroute I comprising:

-   -   a. epoxidizing cyclododecene (CDEN) to epoxycyclododecane (CDAN        epoxide), and    -   b. rearranging the CDAN epoxide to CDON to obtain a mixture        comprising said CDON and cyclododecane (CDAN),        wherein CDAN is separated from the CDON-containing mixture and        oxidized to CDON.

In another embodiment, the present invention relates to a process forsynthesizing laurolactam from CDON, wherein the CDON is prepared asabove.

In yet another embodiment, the present invention relates to a processfor preparing nylon-12 from CDON, wherein the CDON is prepared as above.

BRIEF DESCRIPTION OF THE DRAWING

FIG. 1 shows a flow diagram with the corresponding reactions. Thecompounds in italics are by-products of each reaction.

DETAILED DESCRIPTION OF THE INVENTION

All ranges described hereinafter include all values and subvaluesbetween the lower and higher limits of the given ranges.

A novel process for preparing CDON by a reaction route I has been found,said reaction route I comprising:

-   -   a. epoxidizing cyclododecene (CDEN) to epoxycyclododecane (CDAN        epoxide), and    -   b. rearranging the CDAN epoxide to CDON to obtain a mixture        comprising said CDON and cyclododecane (CDAN),        wherein CDAN is separated from the CDON-containing mixture and        oxidized to CDON (CDON process of the invention).

The CDON process of the invention can be conducted continuously orbatchwise.

The rearrangement is preferably conducted at a maximum hydrogen pressureof 0.9 bar. Preferably, the hydrogen pressure is 0 to 0.9 bar, morepreferably 0 to 0.5 bar. The process according to the invention can beconducted without hydrogen, but it is preferable to initially charge atleast a small hydrogen content to prevent unsaturated by-products. Thishydrogen content may be 0.05 to 0.5 bar, preferably 0.1 to 0.4 bar.

The pressure figures given above relate to the partial pressure ofhydrogen in the system. Typically, components of the reaction mixtureincluding the solvent, air or inert gases such as nitrogen or argon arefurther gaseous constituents of the system.

A rearrangement in the context of the CDON process of the invention isespecially understood to mean a reaction in which at least 90% by weightof CDON, based on the total weight of CDON and CDOL formed, is obtained.

Preferably, the CDEN for the epoxidation (step a) is obtained from CDT.The CDT in turn can be obtained from 1,3-butadiene. The selectivehydrogenation of CDT can be effected in the gas phase with a low partialpressure of hydrogen and a Pd-containing catalyst (EP 1457476). The steptypically gives rise to 5% to 15% by weight of CDAN (cyclododecane) inCDEN.

The epoxidation of CDEN as per step a can be conducted with hydrogenperoxide, by means of a phase transfer catalyst and a metal salt atacidic pH. The CDAN present in the CDEN acts as a phase separationaccelerator (EP 1411050, EP 1411051). After the reaction, CDAN epoxideis obtained, which may further comprise CDAN, unreacted CDEN or both.

CDAN can be at least partly removed prior to the rearrangement (step b).Preferably, this CDAN is oxidized to CDON.

The oxidation of CDAN to CDON may at least partly give rise to CDOL. TheCDOL can then be dehydrogenated to CDON.

The rearrangement as per step b is preferably effected in the presenceof a noble metal catalyst (catalyst system), the catalyst preferablycomprising titanium dioxide, zirconium dioxide or both. This reactionstep forms CDON containing CDAN as by-product (CDON-containing mixture).In addition, CDEN, CDOL or mixtures thereof may be present asby-products. Further by-products having a higher boiling point than CDONmay likewise be present (high boilers). Preferably, the rearrangement isnot conducted in the presence of alkali metal hydroxides as catalyst.

The noble metal in the catalyst system is preferably selected fromruthenium, rhodium, palladium, osmium, iridium and platinum, preferencebeing given to ruthenium, palladium and platinum, and particularpreference to palladium. The noble metal may be in the form of powder(unsupported) or in supported form. Elemental noble metals or oxidesthereof, for example, are suitable in powder form.

In addition, at least one metal oxide may be present as a furtherconstituent of the catalyst system. The metal oxide in the catalystsystem comprises titanium dioxide, zirconium dioxide or mixturesthereof, or consists of at least one of the aforementioned oxides. Thesealso include titanium dioxide- or zirconium dioxide-doped or -coatedsubstances such as alumina or silica.

The metal oxide in the catalyst system may function as a support for thenoble metal in the catalyst system. The noble metal may optionally beapplied to an alternative support selected, for example, from alumina,silica or activated carbon. Titanium dioxide or zirconium dioxide arepreferred supports.

The metal oxides in the catalyst system and the alternative supports maybe in the form of powders or shaped bodies. Suitable shaped bodies arespheres, extrudates, tablets, granules and pellets. It is preferablethat the supports of the noble metal are in the form of shaped bodies.It is likewise preferable that the metal oxide in the catalyst system,if it does not function as a support, is in the form of shaped bodies.

The catalyst system may consequently independently be present as one ofthe following system forms:

-   -   I) The noble metal is unsupported; the metal oxide present in        the catalyst system is at least titanium dioxide or zirconium        dioxide;    -   II) the noble metal is supported, where the support does not        comprise or consist of titanium dioxide and/or zirconium        dioxide. The system additionally comprises at least one metal        oxide selected from titanium dioxide and zirconium dioxide.    -   III) The noble metal is supported on a metal oxide selected from        titanium dioxide and zirconium dioxide, preferably with no        titanium dioxide present.

System forms II and III are preferred, system form III beingparticularly preferred.

Suitable titanium dioxide as a metal oxide in the catalyst system can beobtained by the sulphate process, the chloride process, or by flamehydrolysis (pyrogenic process) of titanium tetrachloride. All theprocesses are known to those skilled in the art. Suitable polymorphs arerutile and anatase, and the titanium dioxide used may comprise mixturesof the polymorphs mentioned.

The titanium dioxide prepared by the sulphate or chloride process maygive an acidic reaction in water, the compounds typically having a pH of3 or less (acidic titanium dioxide). Acidic titanium dioxide likewiseusually contains more than 5% by weight, based on the total weight ofthe titanium dioxide support, of substances such as titanyl sulphate ortitanyl hydroxide. A titanium dioxide based on an acidic titaniumdioxide is commercially available as

Aerolyst 7750 (Evonik, Germany). Acidic titanium oxide is less preferredfor the present process. In other words, it is preferable not to useacidic titanium dioxide. Suitable nonacidic titanium dioxide, which ispreferred, exhibits a pH of 5 or more in water.

Particularly preferred titanium dioxide is obtained by means of flamepyrolysis, as described, for example, in DE-A-830786.

Suitable titanium dioxide is obtainable under the Aeroxide P25 titaniumdioxide (powder) or Aerolyst 7711 (shaped bodies) name from Evonik,Germany, and Hombikat M234 (shaped bodies) from Sachtleben, Germany.

Zirconium dioxide (zirconium(IV) oxide) is obtainable, for example, fromzirconium hydroxide, by calcining it at more than 200° C., for exampleat 350° C. The zirconium dioxide may be doped, for example, with yttriumoxide.

Suitable zirconium dioxide is monoclinic or tetragonal. Mixtures ofthese polymorphs are possible. The metal oxide in the catalyst systemmay have an average bulk density of 0.5 to 2 g/cm³.

The metal oxide in the catalyst system may have a BET surface area of atleast 5 m²/g.

The proportion of noble metal, based on the total weight of noble metaland support, may be 0.01% to 5% by weight, preferably 0.05% to 1.2% byweight and more preferably 0.1% to 0.6% by weight.

The noble metal may be distributed on or within the support.

The molar proportion of noble metal, based on the molar amount of CDANepoxide, may be 0.00001 to 0.1, preferably 0.0001 to 0.01.

The molar proportion of metal oxide in the catalyst system, based on themolar amount of the epoxycyclododecane, may be 0.01 to 100, preferably0.01 to 10.

The CDAN is removed from the reaction mixture and oxidized to CDON.

The remaining mixture comprising CDON and high boilers including CDOLcan be hydrogenated in the presence of hydrogen and a catalyst in orderto remove the unsaturated by-products. Subsequently, the pure CDONproduct is separated from a high boiler fraction including CDOL bydistillation, for example.

CDOL can subsequently be distilled out of this high boiler fraction, andCDOL can be converted to CDON within reaction route I by means of adehydrogenation catalyst. However, it is preferable to send the CDOLremoved, prior to the dehydrogenation, to a reaction route II forpreparation of CDON.

Reaction route II comprises the following steps:

-   -   a. hydrogenation of CDT to CDAN,    -   b. oxidation of CDAN to give a mixture comprising CDOL and CDON        and    -   c. dehydrogenation of CDOL to CDON.

Suitable catalysts for the dehydrogenation of CDOL contain copper orcopper compounds, for example copper(II) oxide.

The CDOL from route I is preferably fed in prior to step c of route II,the dehydrogenation.

In a preferred embodiment of the invention, the CDAN removed from routeI is fed to reaction route II prior to performance of the oxidation. TheCDAN comes from the CDON-containing mixture. CDAN which has been removedafter the epoxidation can be combined with the CDAN from theCDON-containing mixture.

The CDAN can be fed in prior to step b of route II, the oxidation. It ispreferable here for the CDAN to contain up to 0.5% by weight of CDEN,based on the total weight of CDAN and CDEN.

If the CDAN removed from route I contains 0.1% to 99% by weight of CDEN,preferably 0.5% to 99% by weight of CDEN, based on the total weight ofCDAN and CDEN, it is preferable to send this mixture to thehydrogenation of CDT as per step a of reaction route II. In this way,CDEN is hydrogenated to CDAN which can be oxidized in step b of routeII.

With regard to the CDEN content, there is a range of overlap within therange from 0.1% to 0.5% by weight. In this case, the person skilled inthe art can choose whether to send the CDEN-containing CDAN to step a orstep b of route II.

In this respect, reaction routes I and II can be combined in such a waythat CDAN or CDOL obtained are separated and removed from route I andtransferred into route II. It is preferable here to conduct both routescontinuously. This particular embodiment of the invention utilizesby-products from route I for further processing in route II. This isparticularly economically and ecologically beneficial. There is nodisposal of by-products from route I.

The removal of CDEN, CDAN and CDOL and the other high boilers can beundertaken by methods familiar to those skilled in the art. Preferenceis given here to distillation. More preferably, all removals areeffected by means of distillation. It is advantageous to conduct severaldistillations in succession (multistage distillation).

The CDAN can be distilled off after the epoxidation.

After the rearrangement, it is advantageous first to distil off the CDANor a mixture of CDAN and CDEN (low boiler fraction) and to subject theresidue comprising CDON, CDOL and further high boilers to anotherdistillation. In this case, it is possible to obtain CDON which isseparated from a high boiler fraction comprising CDOL. CDOL in turn canbe distilled off from the remaining high boiler products.

Low boilers are substances having a boiling point lower than the boilingpoint of CDON.

FIG. 1 shows a flow diagram with the corresponding reactions. Thecompounds in italics are by-products of each reaction.

Proceeding from CDT, via route I, CDEN is obtained by means ofhydrogenation (selective hydrogenation) and is epoxidized to CDANepoxide. This is followed by a rearrangement to CDON, with removal ofCDAN present—for example by means of distillation. The CDAN presentafter the epoxidation can likewise be removed. The CDAN removed maycontain CDEN. Preferably, the CDAN, however, is sent to therearrangement and removed only after the rearrangement. The CDAN removedis preferably transferred into route II, preferably with combination ofthe individual fractions from route II.

The remaining CDON may contain CDOL which can be removed and fed toroute II. Alternatively, the CDOL can be dehydrogenated within route Ito CDON.

The invention further provides a process for synthesizing laurolactam(lactam process of the invention), in which the aforementioned processof the invention for preparing CDON is employed. In this case, thelaurolactam is obtained from CDON, the CDON being prepared by the CDONprocess of the invention.

The invention further provides a process for synthesising nylon-12(polyamide process of the invention), in which the aforementionedprocess of the invention for preparing CDON is employed.

The CDON produced in the CDON process of the invention can be oximatedin the lactam or polyamide process of the invention to obtaincyclododecanone oxime (CDON oxime). In the subsequent step, the Beckmannrearrangement may be effected to give laurolactam, in which case therearrangement can be effected by means of sulphuric acid or cyanuricchloride. The lactam may be subjected to further processing bypolycondensation to give polyamide.

The oximation, the Beckmann rearrangement and the condensation reactionare known to a person skilled in the art.

Even in the absence of further information it is assumed that a personskilled in the art can make very extensive use of the above description.The preferred embodiments and examples are therefore to be interpretedmerely as descriptive disclosure, and certainly not as disclosure thatis in any way limiting.

The present invention is elucidated in detail hereinafter with referenceto an example. Alternative embodiments of the present invention areobtainable analogously.

Having generally described this invention, a further understanding canbe obtained by reference to certain specific examples which are providedherein for purposes of illustration only, and are not intended to belimiting unless otherwise specified.

EXAMPLES Example 1

Epoxide route=reaction route I

Conventional route=reaction route II

Selective Hydrogenation of CDT

1000 kg/h of CDT were evaporated continuously in a saturation column asgas/liquid contact apparatus at a pressure of 0.75 bar and a temperatureof 155° C. into a 10 m³/h cycle gas stream that consisted essentially ofnitrogen. The resulting gas stream was fed to a fixed bed reactor havinga Pd on Al₂O₃ catalyst, in which the reaction with hydrogen was effectedat a temperature of 130° C. For this purpose, 25 kg/h of hydrogen weremetered into the cycle gas stream at the reactor inlet. At the reactoroutlet, the product was condensed out of the cycle gas stream at 35° C.The condensed liquid had a composition of 84.8% CDEN and 15% CDAN.CDDIEN (cyclododecadiene) and CDT isomers were present in concentrationsof less than 0.2%. The remaining cycle gas stream was fed via acompressor back to the saturation column (see above).

Epoxidation of CDEN:

The mixture of CDEN (84.8%) and CDAN (15%) from the selectivehydrogenation was epoxidized in a three-stage reactor cascade with H₂O₂.The CDAN/CDEN mixture was first metered continuously into a first 8 lreactor at a metering rate of 2 kg/h. Additionally metered into the 5.5l biphasic reaction mixture at a temperature of 80° C. were a 50% H₂O₂solution (544 g/h), an aqueous solution of 30% by weight of Na₂WO₄ and18% by weight of H₃PO₄ (125 g/h), a 50% solution of trioctylamine inCDEN (68 g/h) and water (150 g/h).

The biphasic mixture came from the first reactor with a CDEN conversionof 79% and passed over into a second 8 l reactor. For this purpose, a50% H₂O₂ solution (131 g/h) was metered into the 5.5 l biphasic reactionmixture at a temperature of 78° C.

From this second reactor came a biphasic mixture with a CDEN conversionof 96%, which was passed into a reactor having a fill level of 25 l. Thebiphasic reaction mixture was stirred in this reactor at a temperatureof 76° C. The two phases of the reaction mixture from the 25 l reactorwere separated in a phase separation vessel. The organic phase wassubsequently washed with a 5% NaOH solution (0.5 kg/h) in a 5 l vessel.The two phases were subsequently separated in a separation vessel.

The organic phase was sent to a continuous two-stage distillation. In afirst column (column with 8 m fabric packing; surface area of 500 m²/m³;top pressure 300 mbar), the residual water was removed as distillate.The bottoms were distilled in a second column (column with 6 m fabricpacking; surface area of 500 m²/m³; top pressure 10 mbar), and thedesired product comprising 85%-90% CDAN epoxide and 5%-10% CDAN wasobtained in the distillate at a rate of 2.1 kg/h. This corresponds to anoverall yield of 97% for the epoxidation.

Rearrangement of CDAN Epoxide to CDON

The CDAN epoxide from the preceding step was converted to CDON by meansof a 0.5% Pd/ZrO₂ catalyst in a three-stage reactor cascade. The mixtureof CDAN epoxide (84.8%) and CDAN (15%) from the epoxidation was fed intoa first circulation reactor at a metering rate of 2 kg/h. Thecirculation reactor consisted of a 12 l tubular reactor which was filledwith 10 kg of 0.5% Pd/ZrO₂ fixed bed catalyst at a temperature of 200°C. and was fed from an 8 l reservoir vessel. From the first circulationreactor came a mixture of 59% CDON, 18% CDAN epoxide, 16% CDAN, 0.4%CDEN and 1.9% CDOL. This mixture was metered into a second circulationreactor at a metering rate of 2 kg/h. This second circulation reactorlikewise consisted of an 8 l reservoir vessel and a 12 I tubular reactorwhich was filled with 10 kg of 0.5% Pd/ZrO₂ fixed bed catalyst at atemperature of 200° C.

From the second reaction circuit came a mixture of 73% CDON, 4% CDANepoxide, 16% CDAN, 0.4% CDEN and 2% CDOL. This mixture was metered intoa fixed bed reactor filled with 2.7 kg of Pd/ZrO₂ at a metering rate of2 kg/h. In this tube, the reaction mixture was contacted with N₂ (4 l/h)and H₂ (16 l/h) at a total pressure of 1.7 bar and a temperature of 205°C. From this tube, a crude mixture of 78% CDON, 17% CDAN and 2.2% CDOLwas obtained.

The components of this mixture were separated from one another andpurified by means of distillation.

Distillation of Low Boiler Fraction

The crude mixture from the rearrangement was freed of a low boilerfraction (components having a lower boiling point than CDON) in a firstcontinuous distillation step. The column used was equipped with 8 m offabric packing having a surface area of 500 m²/m³ and was operated at atop pressure of 10 mbar.

The compounds from this low boiler fraction which contain fewer than orequal to 11 carbon atoms were separated from the CDAN in an additionaldistillation column. The CDAN obtained with a purity of 99% wasconducted into the oxidation with boric acid (conventional route).

Distillation of CDON

The bottoms from the first distillation were distilled in a furthercontinuous distillation step (column with 6 m fabric packing; surfacearea of 500 m²/m³), and CDON was obtained as distillate at a toppressure of 10 mbar. Components having a higher boiling point than CDON(for example CDOL) were removed as bottom product. The purity of theCDON obtained was >99% and the CDON yield achieved in the distillationwas 98%.

It was possible to convert this cyclododecanone further to laurolactamby known methods.

The bottoms from this second distillation were purified further in anadditional column: CDOL was separated from other high boilers in anadditional column and conducted into the dehydrogenation (conventionalroute).

Utilization of the CDAN Obtained in the Conventional Route The CDAN (1kg/h) from the epoxide route was reacted with boric acid (0.05 kg/h).With a residence time of 2 h, reaction at 155° C. with oxygen feed rate132 l/h, a CDAN conversion of 8.5% and a selectivity for CDON and CDOLof 88% was obtained. This conversion and the composition corresponded tothe conversion and selectivity from the conventional route. It waspossible to convert the mixture further to laurolactam analogously tothe conventional product.

Utilization of the CDOL Obtained in the Conventional Route

1 kg of CDOL from the epoxide route was mixed with 10 kg of CDOL/CDON(70:30 w:w) mixture from the conventional route in a 30 ldehydrogenation reactor. The reactor was charged with 1.9 kg ofCu-containing catalyst (H10167 from Evonik). After reaction at 240° C.for 6 h, a mixture of CDON (10.5 kg) and CDOL (0.5 kg) was obtained. TheCDON was distilled off with a purity of more than 99.8% and the CDOL wasrecycled into the dehydrogenation. The quality of the CDON obtainedcorresponded to the quality of the cyclododecanone from the conventionalroute, and it was possible to convert it further to laurolactam by thisroute.

Example 2

The CDAN (or the mixture of CDAN and CDEN) can be utilized in analternative way. Instead of transferring the CDAN into the oxidationwith boric acid, it can be used in the preceding stage (hydrogenation ofCDT to CDAN).

This applies particularly when the CDAN from the epoxide route containsa significant amount of CDEN.

Utilization of the mixture of CDAN and CDEN in the CDT hydrogenation:The mixture of CDAN and CDEN (0.04 kg/h) from the epoxide route wasmixed with CDT (0.36 kg/h) in a 0.4 l hydrogenation reactor. Thehydrogenation reactor was charged with 0.284 kg of 0.5% Pd/Al₂O₃. At160° C. and 15 bar of hydrogen, CDAN was obtained with a purity of98.5%. This purity corresponded to the purity of the cyclododecanone inthe conventional route under the corresponding reaction conditions, andit was possible to convert it further to laurolactam by this route.

European patent application EP14179449 filed Aug. 1, 2014, isincorporated herein by reference.

Numerous modifications and variations on the present invention arepossible in light of the above teachings. It is therefore to beunderstood that within the scope of the appended claims, the inventionmay be practiced otherwise than as specifically described herein.

1. A process for preparing cyclododecanone (CDON) by a reaction route I,said reaction route I comprising: a. epoxidizing cyclododecene (CDEN) toepoxycyclododecane (CDAN epoxide), and b. rearranging the CDAN epoxideto CDON to obtain a mixture comprising said CDON and cyclododecane(CDAN), wherein CDAN is separated from the CDON-containing mixture andoxidized to CDON.
 2. The process according to claim 1, wherein therearrangement in step b is effected in the presence of a noble metalcatalyst.
 3. The process according to claim 2, wherein the catalyst forthe rearrangement comprises titanium dioxide, zirconium dioxide or both.4. The process according to claim 1, wherein the CDAN epoxide from stepa comprises CDAN which is at least partly removed prior to therearrangement in step b.
 5. The process according to claim 4, whereinthe CDAN removed prior to the rearrangement is oxidized to CDON.
 6. Theprocess according to claim 1, wherein the CDON-containing mixturecomprises cyclododecanol (CDOL) which is dehydrogenated to CDON.
 7. Theprocess according to claim 6, wherein the CDOL is separated from theCDON-containing mixture prior to the dehydrogenation and is sent to areaction route II for preparation of CDON, said reaction route IIcomprising a. hydrogenation of cyclododecatriene (CDT) to CDAN, b.oxidation of CDAN to give a mixture comprising CDOL and CDON and c.dehydrogenation of CDOL to CDON.
 8. The process according to claim 1,wherein the CDAN removed prior to performance of the oxidation, is sentto a reaction route II for preparation of CDON, comprising a.hydrogenation of CDT to CDAN, b. oxidation of CDAN to give a mixturecomprising CDOL and CDON, and c. dehydrogenation of CDOL to CDON.
 9. Theprocess according to claim 8, wherein the CDAN removed is sent to theoxidation of CDAN as per step b of reaction route II.
 10. The processaccording to claim 9, wherein the CDAN contains up to 0.5% by weight ofcyclododecene (CDEN), based on the total weight of CDAN and CDEN. 11.The process according to claim 8, wherein the CDAN removed is sent tothe hydrogenation of CDT as per step a of reaction route II, the CDANcontaining 0.1% to 99% by weight of CDEN, based on the total weight ofCDAN and CDEN.
 12. The process according to claim 1, wherein at leastone removal of a compound is conducted by distillation.
 13. The processaccording to claim 1, wherein all removals of a compound are conductedby distillation.
 14. A process for synthesizing laurolactam from CDON,wherein the CDON is prepared according to claim
 1. 15. The processaccording to claim 14, wherein the CDON is converted to cyclododecanoneoxime (CDON oxime).
 16. A process for preparing nylon-12 from CDON,wherein the CDON is prepared according to claim 1.